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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:19:45 UTC

Update Date

2022-03-07 02:53:47 UTC

HMDB ID

HMDB0033584

Secondary Accession Numbers

HMDB33584

Metabolite Identification

Common Name

Diethyl tartrate

Description

Diethyl tartrate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Diethyl tartrate is a mild, earth, and fruity tasting compound. Diethyl tartrate has been detected, but not quantified in, alcoholic beverages. This could make diethyl tartrate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Diethyl tartrate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900092D          

 14 13  0  0  0  0            999 V2000
    1.8711   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8724   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033584

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C(O)C(O)C(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3

> <INCHI_KEY>
YSAVZVORKRDODB-UHFFFAOYSA-N

> <FORMULA>
C8H14O6

> <MOLECULAR_WEIGHT>
206.1932

> <EXACT_MASS>
206.07903818

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.82590493124443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-diethyl 2,3-dihydroxybutanedioate

> <ALOGPS_LOGP>
-0.57

> <JCHEM_LOGP>
-0.8233958673333333

> <ALOGPS_LOGS>
-0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.61208687388243

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.187076252689968

> <JCHEM_PKA_STRONGEST_BASIC>
-4.334902326969982

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
45.2488

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethyl tartrate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.493  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.496  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.826  -1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.162  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.827  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.161  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.495  -2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.827  -4.207   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      10.161  -0.357   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.494  -0.357   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.828  -1.897   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   13                                                       
CONECT    4    2   14                                                       
CONECT    5    6    7    9                                                  
CONECT    6    5    8   10                                                  
CONECT    7    5   11   13                                                  
CONECT    8    6   12   14                                                  
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    3    7                                                       
CONECT   14    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0033584
HETATM    1  C1  UNL     1       4.289   0.628  -0.163  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.787  -0.202  -1.318  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.377  -0.287  -1.263  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.738  -0.846  -0.166  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.482  -1.266   0.763  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.256  -0.942  -0.097  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.268  -0.398  -1.264  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.223  -0.189   1.131  1.00  0.00           C  
HETATM    9  O4  UNL     1       0.299  -0.731   2.300  1.00  0.00           O  
HETATM   10  C6  UNL     1      -1.685  -0.175   1.238  1.00  0.00           C  
HETATM   11  O5  UNL     1      -2.268  -0.608   2.266  1.00  0.00           O  
HETATM   12  O6  UNL     1      -2.527   0.307   0.234  1.00  0.00           O  
HETATM   13  C7  UNL     1      -3.941   0.310   0.362  1.00  0.00           C  
HETATM   14  C8  UNL     1      -4.474   0.909  -0.934  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.116   0.068   0.337  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.659   1.601  -0.549  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.468   0.846   0.567  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.033   0.302  -2.282  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.248  -1.233  -1.291  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.102  -1.989  -0.043  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.405  -0.373  -2.004  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.217   0.839   1.043  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.376  -0.084   3.033  1.00  0.00           H  
HETATM   24  H10 UNL     1      -4.286   0.989   1.173  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.355  -0.694   0.557  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.913   1.875  -1.069  1.00  0.00           H  
HETATM   27  H13 UNL     1      -5.550   1.100  -0.904  1.00  0.00           H  
HETATM   28  H14 UNL     1      -4.158   0.243  -1.766  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8   20
CONECT    7   21
CONECT    8    9   10   22
CONECT    9   23
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   24   25
CONECT   14   26   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Diethyl tartric acid	Generator
Diethyl tartrate, (S-(r,r))-isomer	MeSH
Tartaric acid diethyl ester	MeSH
(+)-Diethyl L-tartrate	HMDB
(+)-Diethyl-L-tartrate	HMDB
(+)-Tartaric acid diethyl ester	HMDB
(-)-Diethyl-D-tartrate	HMDB
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, diethyl ester	HMDB
Butanedioic acid, 2,3-dihydroxy- (R-(r,r)), diethyl ester	HMDB
Butanedioic acid, 2,3-dihydroxy-, diethyl ester	HMDB
Diethyl (+)-tartrate	HMDB
Diethyl (2R,3R)-(+)-tartrate	HMDB
Diethyl (2R,3R)-tartrate	HMDB
Diethyl (R,R)(+)tartrate	HMDB
Diethyl 1,2-dihydroxy-1, 2-ethanedicarboxylate	HMDB
Diethyl 1,2-dihydroxy-1,2-ethanedicarboxylate	HMDB
Diethyl 2,3-dihydroxybutanedioate	HMDB
Diethyl 2,3-dihydroxysuccinate	HMDB
Diethyl ester(R,R)-tartaric acid	HMDB
Diethyl L-tartrate	HMDB
Diethyl tartarate	HMDB
Diethyl tartratene	HMDB
Diethyl-D-tartrate	HMDB
Ethyl (+)-tartrate	HMDB
Ethyl tartarate	HMDB
Ethyl tartrate	HMDB
FEMA 2378	HMDB
L-(+)-(Diethyl tartrate)	HMDB
L-(+)-Tartaric acid diethyl ester	HMDB
Racem-dimethoxysuccinic acid, dimethylester	HMDB
Racemic-dimethoxysuccinic acid, dimethyl ester	HMDB
Tartaric acid, diethyl ester	HMDB
Tartaric acid, diethyl ester (8ci)	HMDB
[-]-Tartaric acid diethyl ester	HMDB
1,4-Diethyl 2,3-dihydroxybutanedioic acid	Generator
Diethyl tartrate	MeSH

Chemical Formula

C₈H₁₄O₆

Average Molecular Weight

206.1932

Monoisotopic Molecular Weight

206.07903818

IUPAC Name

1,4-diethyl 2,3-dihydroxybutanedioate

Traditional Name

diethyl tartrate

CAS Registry Number

87-91-2

SMILES

CCOC(=O)C(O)C(O)C(=O)OCC

InChI Identifier

InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3

InChI Key

YSAVZVORKRDODB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Monosaccharide
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Sweat (PMID: 26755145)

Cellular substructure

Extracellular (HMDB: HMDB0033584)
Cytoplasm (HMDB: HMDB0033584)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033584)

Source

Exogenous

Exogenous (HMDB: HMDB0033584)

Food

Food (HMDB: HMDB0033584)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033584)

Biological role

Nutrient (HMDB: HMDB0033584)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	17 °C	Not Available
Boiling Point	280.00 to 281.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	71920 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.29	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	150 g/L	ALOGPS
logP	-0.57	ALOGPS
logP	-0.82	ChemAxon
logS	-0.14	ALOGPS
pKa (Strongest Acidic)	11.19	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	45.25 m³·mol⁻¹	ChemAxon
Polarizability	19.83 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	148.27	31661259
DarkChem	[M-H]-	143.581	31661259
DeepCCS	[M+H]+	143.336	30932474
DeepCCS	[M-H]-	140.978	30932474
DeepCCS	[M-2H]-	175.867	30932474
DeepCCS	[M+Na]+	151.204	30932474
AllCCS	[M+H]+	147.9	32859911
AllCCS	[M+H-H2O]+	144.4	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.2	32859911
AllCCS	[M-H]-	145.1	32859911
AllCCS	[M+Na-2H]-	146.3	32859911
AllCCS	[M+HCOO]-	147.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.97 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7057 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.63 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1499.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	329.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	90.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	385.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	460.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	127.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	807.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	342.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1307.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	253.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	508.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	236.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	155.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethyl tartrate	CCOC(=O)C(O)C(O)C(=O)OCC	2367.8	Standard polar	33892256
Diethyl tartrate	CCOC(=O)C(O)C(O)C(=O)OCC	1281.8	Standard non polar	33892256
Diethyl tartrate	CCOC(=O)C(O)C(O)C(=O)OCC	1426.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diethyl tartrate,1TMS,isomer #1	CCOC(=O)C(O)C(O[Si](C)(C)C)C(=O)OCC	1487.7	Semi standard non polar	33892256
Diethyl tartrate,2TMS,isomer #1	CCOC(=O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)OCC	1571.1	Semi standard non polar	33892256
Diethyl tartrate,1TBDMS,isomer #1	CCOC(=O)C(O)C(O[Si](C)(C)C(C)(C)C)C(=O)OCC	1690.2	Semi standard non polar	33892256
Diethyl tartrate,2TBDMS,isomer #1	CCOC(=O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)OCC	1944.9	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Sweat

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011660

KNApSAcK ID

Not Available

Chemspider ID

13871489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diethyl tartrate

METLIN ID

Not Available

PubChem Compound

62333

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1018981

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Diethyl tartrate (HMDB0033584)

MOL for HMDB0033584 (Diethyl tartrate)

3D MOL for HMDB0033584 (Diethyl tartrate)

3D SDF for HMDB0033584 (Diethyl tartrate)

3D-SDF for HMDB0033584 (Diethyl tartrate)

PDB for HMDB0033584 (Diethyl tartrate)

3D PDB for HMDB0033584 (Diethyl tartrate)

SMILES for HMDB0033584 (Diethyl tartrate)

INCHI for HMDB0033584 (Diethyl tartrate)

Structure for HMDB0033584 (Diethyl tartrate)

3D Structure for HMDB0033584 (Diethyl tartrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized